Who can forget the classic Friends episode where Joey discovers both the stylish allure and unmatched functionality of the Man Bag. Over a decade later, American men continue to struggle with their masculinity and more often than not clump the Man Bag in the same category as messenger bags, satchels and rucksacks. There’s a big difference, and the classic messenger bag is the perfect example.

David Beckham highlights how the brown leather messenger bag is both versatile and classy enough for the businessman on the move (ponytail optional). I have no idea why Beckham’s bag is completely empty in this picture, but it’s roomy enough to fit his balls (soccer). Consider the J Crew Artisan Leather Messenger Bag – $225 at Jcrew.com – Although a bit on the expensive side, it’s a worthy investment, it will never go out of style, and it provides the perfect glove for your beloved Macbook.

John Mayer underscores the biggest fashion trap that continues to befuddle men young and old: You don’t have to match everything! It’s a wonderful canvas messenger bag that no doubt contains racy and lurid pictures of former flame Jennifer Aniston. Unfortunately, it’s hard to let your imagination run wild because John was compelled to wear matching suede shoes and watch band. Sunwashed Canvas messenger Bag – $55 at llbean.com